(3S,4R)-3-<(R)-1'-<(tert-butyldimethylsilyl)oxy>ethyl>-1-<(methoxycarbonyl)methyl>-4-(phenylthio)-2-azetidinone

Base Information

• Chemical Name: (3S,4R)-3-<(R)-1'-<(tert-butyldimethylsilyl)oxy>ethyl>-1-<(methoxycarbonyl)methyl>-4-(phenylthio)-2-azetidinone
• CAS No.: 114156-43-3
• Molecular Formula: C₂₀H₃₁NO₄SSi
• Molecular Weight: 409.622

Synonyms:(3S,4R)-3-<(R)-1'-<(tert-butyldimethylsilyl)oxy>ethyl>-1-<(methoxycarbonyl)methyl>-4-(phenylthio)-2-azetidinone

Chemical Property of (3S,4R)-3-<(R)-1'-<(tert-butyldimethylsilyl)oxy>ethyl>-1-<(methoxycarbonyl)methyl>-4-(phenylthio)-2-azetidinone

Chemical Property:

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Technology Process of (3S,4R)-3-<(R)-1'-<(tert-butyldimethylsilyl)oxy>ethyl>-1-<(methoxycarbonyl)methyl>-4-(phenylthio)-2-azetidinone

There total 3 articles about (3S,4R)-3-<(R)-1'-<(tert-butyldimethylsilyl)oxy>ethyl>-1-<(methoxycarbonyl)methyl>-4-(phenylthio)-2-azetidinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.3%

(3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)-ethyl]-4-phenylthio-2-azetidinone (85281-73-8) + bromoacetic acid methyl ester (96-32-2) → (3S,4R)-3-<(R)-1'-<(tert-butyldimethylsilyl)oxy>ethyl>-1-<(methoxycarbonyl)methyl>-4-(phenylthio)-2-azetidinone (114156-43-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; for 24h; Ambient temperature;

DOI:10.1021/jo00247a005

Reference yield:

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one (76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1) → (3S,4R)-3-<(R)-1'-<(tert-butyldimethylsilyl)oxy>ethyl>-1-<(methoxycarbonyl)methyl>-4-(phenylthio)-2-azetidinone (114156-43-3)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol

2: 89.3 percent / potassium carbonate / dimethylformamide / 24 h / Ambient temperature

With potassium carbonate; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00247a005

Reference yield:

sodium thiophenolate (930-69-8) → (3S,4R)-3-<(R)-1'-<(tert-butyldimethylsilyl)oxy>ethyl>-1-<(methoxycarbonyl)methyl>-4-(phenylthio)-2-azetidinone (114156-43-3)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol

2: 89.3 percent / potassium carbonate / dimethylformamide / 24 h / Ambient temperature

With potassium carbonate; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00247a005

upstream raw materials:

(3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)-ethyl]-4-phenylthio-2-azetidinone

bromoacetic acid methyl ester

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

sodium thiophenolate

Downstream raw materials:

methyl (3S,4R)-3-<<(R)-1'-<(tert-butyldimethylsilyl)oxy>ethyl>-2-oxo-4-(phenylthio)-5-azetidinyl>-4-pentenoate

2-Allyl-2-{(3S,4R)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-phenylsulfanyl-azetidin-1-yl}-pent-4-enoic acid methyl ester

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